Bromine → N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamide

HRID 1487201

반응식

HRID 1487201 반응식
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=[CH:10][C:2]1=2.[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:10]1[C:2]2[O:1][CH2:6][CH2:5][O:4][C:3]=2[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=1

참가 물질

4

반응물 2

HCID 24408BromineHCID 658593N-(2,3-dihydro-1,4-benzodioxin-5-yl)acetamide

생성물 1

HCID 23269228N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamide수율 64.5%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of N-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide (5.5 g, 28.5 mmol) in chloroform (20 mL) cooled at −20° C. was slowly added a solution of bromine (1.6 mL, 30 mmol) in chloroform (5 mL) so that the reaction temperature was maintained below −10° C. The reaction was stirred at 0° C. for 10 minutes, and then quenched immediately with water. The mixture was extracted with dichloromethane; the combined extracts were washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (dichloromethane) to afford the product N-(8-bromo-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide (5 g, yield 64%). 1H NMR (400 MHz, CDCl3) δ ppm 9.23 (s, 1H), 7.46-7.48 (d, 1H, J=8.8 Hz), 7.04-7.06 (d, 1H, J=9.2 Hz), 4.32-4.40 (m, 4H), 2.07 (s, 3H).

후처리

  1. temperaturewas maintained below −10° C
  2. customquenched immediately with water
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe combined extracts were washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-998f2ee94ffd4bcf99e63d2f61b440e5
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428508B2

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